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dc.contributor.author
Colomer, Juan Pablo
dc.contributor.author
Mayordomo, María Ángeles Canales
dc.contributor.author
De Toro, Beatriz Fernández
dc.contributor.author
Jiménez Barbero, Jesús
dc.contributor.author
Varela, Oscar Jose
dc.date.available
2018-06-28T19:47:05Z
dc.date.issued
2015-02
dc.identifier.citation
Colomer, Juan Pablo; Mayordomo, María Ángeles Canales; De Toro, Beatriz Fernández; Jiménez Barbero, Jesús; Varela, Oscar Jose; Thiodisaccharide sulfoxides: Absolute configuration of the so sulfur atom and influence on the biological activity towards the β-galactosidase from E. coli; Wiley VCH Verlag; European Journal of Organic Chemistry; 2015; 7; 2-2015; 1448-1455
dc.identifier.issn
1434-193X
dc.identifier.uri
http://hdl.handle.net/11336/50484
dc.description.abstract
Benzyl 3-deoxy-4-S-(β-D-galactopyranosyl)-4-thio-β-D-threopentopyranoside (3) is a potent inhibitor of the β-galactosidase from Escherichia coli synthesized in our laboratory. The 2′,3′,4′,6′-tetra-O-acetyl derivative of this thiodisaccharide was oxidized with m-chloroperoxybenzoic acid to give a 2:1 diastereomeric mixture of sulfoxides 2S and 2R. The absolute configurations of their sulfur stereocenters were determined by using NMR techniques and by taking into account the anisotropic effects of the S=O group in the major conformers. O-Deacetylation of 2S and 2R afforded the free thiodisaccharide S-oxides 4S and 4R, which were evaluated as inhibitors of the above-mentioned enzyme. The kinetic studies showed that 4S and 4R are competitive inhibitors of the enzyme with Ki values of 0.19 and 0.45 mM, respectively. Further enzymatic reactions demonstrated that 4S is also a substrate of the β-galactosidase, as it was diastereoselectively hydrolyzed, with 4R remaining unchanged under the same conditions.
dc.format
application/pdf
dc.language.iso
eng
dc.publisher
Wiley VCH Verlag
dc.rights
info:eu-repo/semantics/openAccess
dc.rights.uri
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.subject
Biomimetics
dc.subject
Carbohydrates
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Configuration Determination
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Enzymes
dc.subject
Inhibitors
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Sulfoxides
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Otras Ciencias Químicas
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Ciencias Químicas
dc.subject.classification
CIENCIAS NATURALES Y EXACTAS
dc.title
Thiodisaccharide sulfoxides: Absolute configuration of the so sulfur atom and influence on the biological activity towards the β-galactosidase from E. coli
dc.type
info:eu-repo/semantics/article
dc.type
info:ar-repo/semantics/artículo
dc.type
info:eu-repo/semantics/publishedVersion
dc.date.updated
2018-04-27T13:28:04Z
dc.journal.volume
2015
dc.journal.number
7
dc.journal.pagination
1448-1455
dc.journal.pais
Alemania
dc.journal.ciudad
Weinheim
dc.description.fil
Fil: Colomer, Juan Pablo. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
dc.description.fil
Fil: Mayordomo, María Ángeles Canales. Universidad Complutense de Madrid. Facultad de Ciencias Químicas; España
dc.description.fil
Fil: De Toro, Beatriz Fernández. Consejo Superior de Investigaciones Científicas. Centro de Investigaciones Biológicas; España
dc.description.fil
Fil: Jiménez Barbero, Jesús. Consejo Superior de Investigaciones Científicas. Centro de Investigaciones Biológicas; España
dc.description.fil
Fil: Varela, Oscar Jose. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Centro de Investigaciones en Hidratos de Carbono. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Centro de Investigaciones en Hidratos de Carbono; Argentina
dc.journal.title
European Journal of Organic Chemistry
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/doi/http://dx.doi.org/10.1002/ejoc.201403609
dc.relation.alternativeid
info:eu-repo/semantics/altIdentifier/url/https://onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201403609
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